2-Bromothiazole → 5-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HRID 1297307Notes

Reaction equation

HRID 1297307 reaction equation
C(O[C@H]1CN(C2N=CC=CN=2)C[C@H]1NC1C(CC)=NC(C2C(C)=NC(OC)=CC=2)=C(CC)N=1)C.Br[C:36]1[S:37][CH:38]=[CH:39][N:40]=1.[CH3:41][N:42]([CH3:69])[C:43]1[N:48]=[CH:47][C:46]([C:49]2[N:50]=[C:51]([CH2:66][CH3:67])[C:52]([NH:57][C@H:58]3[C@@H:62]([O:63][CH2:64][CH3:65])[CH2:61][NH:60][CH2:59]3)=[N:53][C:54]=2[CH2:55][CH3:56])=[C:45]([CH3:68])[CH:44]=1>>[CH3:69][N:42]([CH3:41])[C:43]1[N:48]=[CH:47][C:46]([C:49]2[N:50]=[C:51]([CH2:66][CH3:67])[C:52]([NH:57][C@H:58]3[C@@H:62]([O:63][CH2:64][CH3:65])[CH2:61][N:60]([C:36]4[S:37][CH:38]=[CH:39][N:40]=4)[CH2:59]3)=[N:53][C:54]=2[CH2:55][CH3:56])=[C:45]([CH3:68])[CH:44]=1

Participants

4

Reactant 3

HCID 764302-BromothiazoleHCID 11374683N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amineHCID 58914568HCID 58914568, compound

Product 1

HCID 114657955-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Procedure

Following the procedure for the preparation of N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine but substituting 2-bromo-1,3-thiazole and 5-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ) 7.99, 7.23, 6.53, 6.46, 5.20, 4.92, 4.29, 4.02, 3.78, 3.58, 3.42, 3.13, 2.71, 2.53, 2.12, 1.33–1.27, 1.16; IR (diffuse reflectance) 2970, 2931, 2872, 2350 (w), 1606 (s), 1537 (s), 1489 (s), 1393 (s), 1372, 1360, 1347, 1343, 1338, 1210, 1122 cm−1 HRMS (ESI) calcd for C25H35N7OS+H1 482.2702. found 482.2699.

Sources & evidence

ORD record
ord-031d85a341c34eb18e0ccf14c8868469
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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